Process of accelerating rubber vulcanization and product thereof



Patented June 19, 1928.

UNITED STATES PATENT OFFICE.

DONALD H. POWERS, OF PENNS GROVE, NEW JERSEY, ABSIGNOR TO E. I. DU PONTDE NEMOUIES & COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF DELA-WARE.

PROCESS OF ACOELERATING RUBBER 'VULCANIZATION AND PRODUCT THEREOF.

1V0 Drawing. Application filed July 28,

This invention relates to the vulcanization of rubber in the presence ofcertain organic accelerators and to the rubber product resultingtherefrom.

It is well known that the salts of alkyl xanthogenic acids and theiroxidation prodnote, the oxythiocarbonic disulphides are rather activeaccelerators of vulcanization. However, their use requires special care,for vulcanization at temperatures as low as 70 C. has been obtained.This tendency to prevulcanize or scorch limits very greatly the use ofthe xanthogenates and their oxidation products.

It is an object of this invention to provide a new vulcanizing processbased on the use of substances prepared from relatively cheapintermediates and which show less tendency to prevulcanize than theclasses of compounds mentioned above. It is another object of thisinvention to provide a new vulcanizing process that can be conducted attemperatures below 250 F.,thus making it possible to obtain rubberstocks of high physical properties, inasmuch as it is not necessary toheat the rubber to the usual hi h temperatures to effect vulcanization.fihe new compositions of matter that I have found to be particularlyvaluable as accelerators for the vulcanization of rubber or rubber-likesubstances may be prepared in the following manner where R=an alkyl grouor substituted alkyl X=a halogen ra ical.

The new compositions formed have been called Ualkyl thiocarbonicmonosulphides A referred method of preparing them is as to lows:

One hundred and seventy pounds of sodium butyl xanthogenate aredissolved in five hundred pounds of water. Fifty-three pounds ofcyanogen bromide are melted and slowly run into the cooled, agitatedwater solution of sodium butyl xanthogenate. The reaction is almostinstantaneous and 0.5 hour after all of the cyanogen bromide has beenrun into the solution the oxybutylthio- 1926. Serial No. 125,598.

It has been found that the oxy alkyl thio carbonic monosulphides arestill more effective accelerators of vulcanization in the presence ofammonia or amines. In a stock containing one hundred parts of rubber,three parts of sulfur, three parts of zinc oxide, and three parts of oxyethyl thio carbonic monosulphide, a cure was obtained at 100 C. at theend of ninety minutes. When the same stock was used and one part ofaniline Iwas added a good cure was obtained in an our.

It is understood that I do not wish to be limited to the process hereinoutlined nor to the cases mentioned, for it will be obvious to thoseskilled in the art that it is not so limited but that variousmodifications and changes may be made therein, without deartin from thespirit of the invention or rom t e scope of the appended claims.

I claim:

1. A process for accelerating the vulcanizing of rubber which comprisesvulcanizing the same in the presence of a material embodying thefollowing organic structure:

s a no-o -s- -o-o-a' where R and R represent an alkyl group.

2. A process for accelerating the vulcanization of rubber whichcomprises vulcanizing the same in the presence of a thio carbonicmonosulphide derivative.

3. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine and a material embodying the followingorganic structure:

s s R--0 -c-so--o n' where R and R represent an alkyl group.

4. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine and a derivative of thio carbonicmonosulphidc.

5. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent and the product obtainedby the interaction of asalt of an alkyl xanthogenate with a cyanogen halide.

6. A process for accelerating the vulcanization of rubber whichcomprises vulcanizing the same in the presence of oxy ethyl thiocarbonic monosulphidc.

7. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine, and oxy ethyl thio carbonicmonosulphide.

8. A process for accelerating the vulcanization of rubber whichcomprises vulcanizing the same in the presence of oxy butyl thiocarbonic monosulphidc.

9. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine, and oxy butyl thio carbonicmonosulphide.

10. A rubber product which has been vulcanized in the presence of amaterial embodying the following organic structure:

tuted alkyl groups.

11. A rubber product which has been vulcanized in the presence of a thiocarbonic monosulphide derivative.

12. A rubber product which has been vulcanized in the presence of avulcanizing agent, an amine and a material embodying the followingorganic structure:

where R and R represent an alkyl or substituted alkyl group.

13. A rubber product which has been vulcanized in the presence of avulcanizing agent, an amine, and a derivative of thio carbonicmonosulphidc.

14. A rubbe product which has been Vulcanized in the presence of theproduct obtained by the interaction of a salt of an alkyl xanthogenatewith a cyanogen halide.

15. A rubber product which has been vulcanized in the presence of oxyethyl thio carbonic monosulphidc.

16. A'rubber product which has been vul canized in the presence of avulcanizing agent, an anime, and oxy ethyl thio carbonic monosulphidc.

17. A rubber product which has been vulcanized in the presence of oxybutyl thio carbonic monosulphide.

18. A rubber product which has been vulcanized in the presence of avulcanizing agent, an amine, and oxy butyl thio carbonic monosulphidc.

In testimony whereof I affix my signature.

DONALD H. POWERS.

CERTIFICATE OF CORRECTION.

Patent No. l, 674, 122.

Granted June 19, 1928, to

DONALD H. POWERS.

It ishereby certified that error appears in the printed specification ofthe above numbered patent requiring correction as follows:

Page 2, lines 33 and 34,

' claim 10, in the formula, strike out the doublc bondhetween the."0 andR" and insert instead a single bond; and that the said Letters Patentshould be read with this correction therein that the same may conform tothe record of the case in the Patent Off ice.

Signed and sealed this 31st day of July, A. D. 1928.

(Seal) M. J. Moore, Acting Commissioner of Patents.

embodying the following organic structure:

s s R--0 -c-so--o n' where R and R represent an alkyl group.

4. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine and a derivative of thio carbonicmonosulphidc.

5. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent and the product obtainedby the interaction of asalt of an alkyl xanthogenate with a cyanogen halide.

6. A process for accelerating the vulcanization of rubber whichcomprises vulcanizing the same in the presence of oxy ethyl thiocarbonic monosulphidc.

7. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine, and oxy ethyl thio carbonicmonosulphide.

8. A process for accelerating the vulcanization of rubber whichcomprises vulcanizing the same in the presence of oxy butyl thiocarbonic monosulphidc.

9. A process for treating rubber which comprises subjecting the rubberto a vulcanizing agent, an amine, and oxy butyl thio carbonicmonosulphide.

10. A rubber product which has been vulcanized in the presence of amaterial embodying the following organic structure:

tuted alkyl groups.

11. A rubber product which has been vulcanized in the presence of a thiocarbonic monosulphide derivative.

12. A rubber product which has been vulcanized in the presence of avulcanizing agent, an amine and a material embodying the followingorganic structure:

where R and R represent an alkyl or substituted alkyl group.

13. A rubber product which has been vulcanized in the presence of avulcanizing agent, an amine, and a derivative of thio carbonicmonosulphidc.

14. A rubbe product which has been Vulcanized in the presence of theproduct obtained by the interaction of a salt of an alkyl xanthogenatewith a cyanogen halide.

15. A rubber product which has been vulcanized in the presence of oxyethyl thio carbonic monosulphidc.

16. A'rubber product which has been vul canized in the presence of avulcanizing agent, an anime, and oxy ethyl thio carbonic monosulphidc.

17. A rubber product which has been vulcanized in the presence of oxybutyl thio carbonic monosulphide.

18. A rubber product which has been vulcanized in the presence of avulcanizing agent, an amine, and oxy butyl thio carbonic monosulphidc.

In testimony whereof I affix my signature.

DONALD H. POWERS.

CERTIFICATE OF CORRECTION.

Patent No. l, 674, 122.

Granted June 19, 1928, to

DONALD H. POWERS.

It ishereby certified that error appears in the printed specification ofthe above numbered patent requiring correction as follows:

Page 2, lines 33 and 34,

' claim 10, in the formula, strike out the doublc bondhetween the."0 andR" and insert instead a single bond; and that the said Letters Patentshould be read with this correction therein that the same may conform tothe record of the case in the Patent Off ice.

Signed and sealed this 31st day of July, A. D. 1928.

(Seal) M. J. Moore, Acting Commissioner of Patents.

